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Activities and Awards
Gencorp Award for Excellence in Chemical Synthesis, 2000
Research Corporation, Research Innovation Award, 1999
National Science Foundation Career Award 1999-2003
National Institutes of Health, First Award, 1998-2002
Research Interests
Our primary interest lies in the field of chemical synthesis. Within this
discipline, we are particularly facinated by the interplay between structure
(biological activity), total synthesis, and reaction development.
Total Synthesis and Structure
Biologically active targets that are currently receiving attention in our laboratory include: (a) fused polycyclic ether natural products (e.g. gambierol, gambieric acid, psymberin); (b) indoline and oxindole natural products (e.g. perophoramidine, communesin B); (c) oxygenated cembranoid natural products (eleutherobin, eunicellins, labiatins); (d) the general class of indolizidine and pyrrolizidine alkaloids; (e) others.
 Reaction Development
We are equally involved in reaction development with a particular emphasis on the use of new and/or improved methods to the synthesis of the targets mentioned above. Reactions that are currently being examined in our laboratory include: (a) new methods to synthesize carbon-glycosides; (b) enol ether-olefin ring-closing metathesis reactions to fused polycyclic ethers; (c) the use of rhodium carbenoids to generate highly substituted indoles and indolines; (d) anionic fragmentation and condensation reactions of bicyclic ring systems; (e) tandem ring-opening/cross metathesis (ROCM) and ring-opening/ring-closing metathesis (RORCM) reactions of norbornenes.
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Selected Publications
- Johnson, H. W. B.; Majumder, U.; Cox, J. M.; Rainier, J. D. "The Total Synthesis of Gambierol"
- Liu, Z.; Rainier, J. D. "Ring-Opening/Cross-Metathesis Reactions of Norbornenes with Electron Rich Olefins"
- Nyong, A. M.; Rainier, J. D. "The Diastereoselective Synthesis of Quaternary Substituted Thioindolines from Sulfur Ylide Intermediates,"
- Roberts, S. W.; Rainier, J. D. "Substitution and Remote Protecting Group Influence on the Oxidation/Addition of Substituted 1,2-Anhydroglycosides: A Novel Entry into C-Ketosides"
- Majumder, U.; Rainier, J. D. "Olefin Metathesis/Carbonyl Olefination using the Takai, Utimoto Reduced Titanium Alkylidene. An Efficient Entry into Cyclic Enol Ethers"
Published
- Weerasakere, M.; Liu.; Rainier, J. D. "Highly Regioselective Ring-Opening/Cross-Metathesis Reactions of 2-Sulfonylnorbornene Derivatives," Org. Lett. 2004 , 6 , 1625.
- Novikov, A. N.; Kennedy, A. R.; Rainier, J. D. "Sulfur Ylide Initiated Thioclaisen Rearrangements. The Synthesis of Highly Substituted Indolines," J. Org. Chem. 2003 , 68 , 993-996.
- Novikov, A. N.; Sabahi, A.; Nyong, A. M.; Rainier, J. D. "The diastereoselective Synthesis of Quaternary Substituted Indolines from Sulfur Ylide Intermediates", Tetrahedron Asymm. 2003 14 , 911-915 .
- Majumder, U.; Cox, J. M.; Rainier, J. D. "Synthesis of an F-H Gambierol Subunit Using a C-Glycoside Centered Strategy," Org. Lett. 2003 5 , 913-916.
- Weerasakere, M.; Xu, Q.; Rainier, J. D. "An Anionic Condensation and Fragmentation Approach to 3-Pyrrolines" Tetrahedron Lett. 2002 , 43 , 8913.
- Allwein, S. P.; Cox, J. D.; Howard, B., E.; Johnson, H., W, B.; Rainier, J. D. " C -Glycosides to Fused Polycyclic Ethers" Tetrahedron 2002 , 58 , 1997.
- Imbriglio, J. E.; Rainier, J. D. "[2+2+1] Cycloadditions of Ynol Ethers. The Synthesis of Iron Complexes of 3-Alkoxycyclopentadienones" Tetrahedron Lett. 2001 , 42 , 6987.
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